Established at the outset of the punk rock boom, Stiff Records signed various punk and new wave acts such as Nick Lowe, The Damned, Lene Lovich, Wreckless Eric, Plummet Airlines, Elvis Costello, Ian Dury and Devo. The label's marketing and advertising was often provocative and witty billing itself as "The World's Most Flexible Record Label". Other slogans were "We came. We saw. We left", "If It Ain't Stiff, It Ain't Worth a Fuck", and "When You Kill Time, You Murder Success" (printed on promotional wall clocks). On the label of Stiff's sampler compilation Heroes & Cowards was printed: "In '78 everyone born in '45 will be 33-1/3". A very early Stiff sampler album, A Bunch of Stiff Records, introduced the slogan, "If they're dead, we'll sign them" and "Undertakers to the Industry".

Stiff also produced eccentric but highly effective promotional campaigns, such as the three package tours in 1977 (Live Stiffs), 1978 (Be Stiff) and 1980 (Son Of Stiff), Elvis Costello's "busking outside CBS Records" arrest and the at least 29 different wallpaper sleeves printed for Ian Dury's second album, Do It Yourself, with associated unscheduled makeovers of unsuspecting record shops.

Barney Bubbles was responsible for much of the graphic art associated with the early Stiff releases.

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Robinson and Riviera were well-known London music business characters. Robinson had briefly worked for Jimi Hendrix in the late 1960s and also managed pub rock combo Brinsley Schwarz in the early 1970s, and Jakeman had been an early manager for another pub rock band, Dr. Feelgood, from Essex. The label was started with a loan of £400 from Lee Brilleaux of Dr. Feelgood.

Stiff found quick success. Its first release, on 14 August 1976, was a single (in the normal 7" vinyl 45 rpm format) by Nick Lowe, "So It Goes", B-side "Heart Of The City", with the striking catalogue number BUY 1.[1][2] That record sold 10,000 copies, but Stiff's next release, "Between The Lines" by Pink Fairies, sold only around half of that.[3] Robinson and Riviera used money from their Advancedale management company to finance the release of what is generally accepted as the United Kingdom's first punk single, "New Rose" by The Damned, in November 1976 which was a veritable hit.

November 1976 also saw the release of a single by Nottingham-based band Plummet Airlines 'Silver Shirt'/'This is the World'. Plummet Airlines then went on to be featured on the John Peel show in May and August 1977, as well as releasing the album 'On Stony Ground' on Armageddon Records in 1981. Early in 1977, Stiff Records picked up speed, signing Wreckless Eric, Ian Dury, and Elvis Costello. Bigger sales followed, and a distribution deal with Island Records and EMI was set up. Each release was given individual attention, with inventive artwork, picture sleeves and a range of snappy slogans, often coupled with inventive marketing campaigns that achieved the label a great deal of publicity, if not always huge profit margins.

Robinson and Riviera were a fiery management combination, and after a series of disagreements, Riviera left Stiff in early 1978 to form the short-lived Radar Records, taking Elvis Costello, Nick Lowe and Yachts with him as a settlement package. Riviera's departure coincided with the end of the "5 Live Stiffs Tour", which showcased emerging star Ian Dury. Dury's album New Boots & Panties had raced up the charts and its sales kept the label in business over the following months. In 1979, Robinson signed Madness, whose considerable commercial success, both in Britain and abroad, would keep Stiff afloat for several years.

The next few years were the halcyon period, with many Top 20 single chart placings, including the label's first No. 1 single, "Hit Me with Your Rhythm Stick" by Ian Dury, and a number of other big-selling albums. Stiff expanded rapidly and moved its premises twice. It also continued to release dozens of obscure and uncommercial releases. For example The Wit & Wisdom of Ronald Reagan, was an LP that was completely silent on both sides, which sold over 30,000 copies, on Magic Records, with its own slogan, "If it sells, it must be Magic".

At the end of 1983, Island Records bought 50% of Stiff, and Robinson ran both labels. Island was very short of money at the time and Robinson had to lend it £1,000,000 to fund the share purchase and pay the payroll. Nonetheless, Robinson led Island through their best year ever[clarification needed], with, among others releases by Frankie Goes to Hollywood, Legend by Bob Marley, and U2's The Unforgettable Fire. Stiff signed The Pogues, but then Madness left under a cloud. The Island deal failed and Dave Robinson regained control of the newly independent label in 1985. Hits by The Pogues and Furniture helped Stiff to survive another twenty months, but the underlying causes for the failure of the Island deal finally became too burdensome for Stiff and it was sold to ZTT. Warner Music Group holds the rights currently to Stiff's masters and most are reissued through Rhino Entertainment .

In 2007, ZTT and its parent company SPZ Group reactivated the label.[4] Stiff quickly broke one of the UK's hottest new indie acts, The Enemy. It then released a string of well-received albums of new work from legacy Stiff artists, including as Wreckless Eric, Henry Priestman, Any Trouble, and Chris Difford. Brand new acts signed to the label included The Tranzmitors and Eskimo Disco. Swedish designer Tobbe Stuhre[5] was appointed official Stiff Records designer.

In 2008, Union Square Music released The Big Stiff Box Set. This detailed catalogue release contained 98 tracks across four CDs and the 100-page The Big Stiff Book by music journalist and Stiff expert, Ian Peel.

Robinson and Riviera had arranged package tours ‒ such as the 1975 Naughty Rhythms tour ‒ for acts they managed before forming Stiff. The first tour, known as the Live Stiffs Tour or 5 Live Stiffs (3 October – 5 November 1977), comprised five bands: Elvis Costello and The Attractions, Ian Dury and the Blockheads, Wreckless Eric and The New Rockets, Nick Lowe's Last Chicken in the Shop, and Larry Wallis's Psychedelic Rowdies. Having signed all the named artists as individuals, bands had to be formed in order to tour: these were largely based on the session musicians used for the artists' solo records. There were 18 musicians on the tour, several doubling up, e.g. Dury playing drums for Wreckless Eric while the last two "bands" had the same line up (Nick Lowe, Larry Wallis, Dave Edmunds, Terry Williams, Pete Thomas and Penny Tobin). A documentary of the tour, titled "If It Ain't Stiff..." (directed by Nick Abson, produced by Angela Saunders, photographed by Mike Miles with sound by Neville Wills) was made by Rockflicks and has been used extensively by the BBC and others.

The original idea was that the running order would rotate each night, but Dury and Costello were clearly the strongest acts. Costello played mostly new material and cover versions, rather than numbers from his recently released album My Aim is True, so the gigs usually ended with most of the artists on stage performing Dury's "Sex & Drugs & Rock & Roll". A live album entitled Live Stiffs Live and a video of the tour were produced, but the tour only covered the UK.[6]

After the departure of Riviera, Robinson arranged a second tour, the Be Stiff or the Be Stiff Route 78 tour, from October to November 1978 (UK), again comprising five acts; Wreckless Eric, Lene Lovich, Jona Lewie, Mickey Jupp, and Rachel Sweet. The mainland section of the UK tour was undertaken by train and the Irish section by coach, and then continued on to the USA, without Jupp, who was afraid of flying. The artists contributed to an EP with cover versions of the Devo song, and early Stiff single, "Be Stiff".[7]

The final tour, the Son of Stiff Tour 1980, comprised Ten Pole Tudor, Any Trouble, Dirty Looks, Joe "King" Carrasco and the Crowns, and The Equators. Undertaken by bus, this European tour was not successful.[8] The tour led to a 12" EP Son of Stiff Tour 1980 (SON 1) [9] and a short movie directed by Jeff Baynes. The movie has not been released for sale, but was shown on BBC4 in September 2006.[10]